Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 75 rentals matching your search criteria
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Sundown Refuge

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently remodeled, tastefully decorated. This rental is hard to beat!

Paradise Place

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Bogey's Retreat

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.

Coral Palm

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock located on Stock Island.

Linger Longer

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Just imagine stepping out of the rental and stepping right into the pool!

Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath, 2-story town home, located in the President's Walk of Truman Annex.

First Breath

Type

  • House
Old Town
3 Bedrooms
2 Baths
6 Guests

Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

Paradise Palms

Type

  • House
Old Town
2 Bedrooms
2 Baths
6 Guests

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

Coral Garden

Type

  • Townhouse
Stock Island
2 Bedrooms
2.5 Baths
4 Guests

For those looking for a cozy little getaway on a budget - Coral Garden is the answer!

Lazy Gecko

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

Truman's Hideaway

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

Coral Villa

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!

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